Thiophosgene → 7-Isothiocyanatobenzofuran

HRID 848805Notes

Reaction equation

HRID 848805 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:11](Cl)(Cl)=[S:12]>Cl>[N:1]([C:2]1[C:7]2[O:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[C:11]=[S:12]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 11217277Benzofuran-7-amine

Product 1

HCID 130352777-Isothiocyanatobenzofuran

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

7-Amino-benzo[b]furan is reacted with thiophosgene in 3 N hydrochloric acid at room temperature over 1 hour to give 7-isothiocyanatobenzo[b]furan. (M.Pt. 45°-46° from petroleum ether.) Reaction of this isothiocyanate with ethanolamine in ether gives N-benzo[b]furan-7-yl-N'-2-hydroxyethylthiourea (m.pt. 138°-139° from methanol) which is used further in the crude state.

Sources & evidence

ORD record
ord-de60e94b7312446a8c937ef65e6104c9
Source dataset
uspto-grants-1981_10
Patent number
US04297490

Reaction notes

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